IL26021A - Chroman-8-yl-carbamates,preparation thereof and pesticidal compositions containing them - Google Patents
Chroman-8-yl-carbamates,preparation thereof and pesticidal compositions containing themInfo
- Publication number
- IL26021A IL26021A IL26021A IL2602166A IL26021A IL 26021 A IL26021 A IL 26021A IL 26021 A IL26021 A IL 26021A IL 2602166 A IL2602166 A IL 2602166A IL 26021 A IL26021 A IL 26021A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- chromanyl
- group
- hydrogen
- dimethyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 52
- 230000000361 pesticidal effect Effects 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 19
- -1 compound 2,2-dimethyl-8-chromanyl methyl-carbamate Chemical class 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 11
- 241000244206 Nematoda Species 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- ZLHCKBFKIBDNSR-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromen-8-ol Chemical compound C1=CC(O)=C2OC(C)(C)CCC2=C1 ZLHCKBFKIBDNSR-UHFFFAOYSA-N 0.000 claims description 6
- NUXKGYKGLAUDHN-UHFFFAOYSA-N 3,4-dihydro-2H-chromen-8-yl carbamate Chemical class C(N)(OC=1C=CC=C2CCCOC12)=O NUXKGYKGLAUDHN-UHFFFAOYSA-N 0.000 claims description 6
- 241000238421 Arthropoda Species 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- 101100021159 Bacillus subtilis (strain 168) lgt gene Proteins 0.000 claims 1
- 241001225883 Prosopis kuntzei Species 0.000 claims 1
- 101100175379 Streptomyces sp gerF gene Proteins 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229940126543 compound 14 Drugs 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 15
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
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- UZQMSSMXIUODQW-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-8-ol Chemical compound C1CCOC2=C1C=CC=C2O UZQMSSMXIUODQW-UHFFFAOYSA-N 0.000 description 8
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- 231100000167 toxic agent Toxicity 0.000 description 7
- 239000003440 toxic substance Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- 241000196324 Embryophyta Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
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- 229910052760 oxygen Inorganic materials 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 230000001069 nematicidal effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- XAMLYVOKCFEFDG-UHFFFAOYSA-N (2,2-dimethyl-3,4-dihydrochromen-8-yl) n-methylcarbamate Chemical compound C1CC(C)(C)OC2=C1C=CC=C2OC(=O)NC XAMLYVOKCFEFDG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 241000257226 Muscidae Species 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- OPJJOMIPHKFUKV-UHFFFAOYSA-N 2,2-diethyl-3,4-dihydrochromene Chemical compound C1=CC=C2OC(CC)(CC)CCC2=C1 OPJJOMIPHKFUKV-UHFFFAOYSA-N 0.000 description 3
- MITIYLBEZOKYLX-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromene Chemical compound C1=CC=C2OC(C)(C)CCC2=C1 MITIYLBEZOKYLX-UHFFFAOYSA-N 0.000 description 3
- PMBSJQIGLMSEKN-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-8-yl n-methylcarbamate Chemical compound C1CCOC2=C1C=CC=C2OC(=O)NC PMBSJQIGLMSEKN-UHFFFAOYSA-N 0.000 description 3
- CTRTZLJYANJCHF-UHFFFAOYSA-N 8-hydroxy-2,3-dihydrochromen-4-one Chemical compound O=C1CCOC2=C1C=CC=C2O CTRTZLJYANJCHF-UHFFFAOYSA-N 0.000 description 3
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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- NFKGQADZUSBYGI-UHFFFAOYSA-N 2,2,5-trimethyl-3,4-dihydrochromene Chemical compound O1C(C)(C)CCC2=C1C=CC=C2C NFKGQADZUSBYGI-UHFFFAOYSA-N 0.000 description 2
- BKSZMIWJCKZSGU-UHFFFAOYSA-N 2,2-diethyl-3,4-dihydrochromen-8-ol Chemical compound C(C)C1(OC2=C(C=CC=C2CC1)O)CC BKSZMIWJCKZSGU-UHFFFAOYSA-N 0.000 description 2
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- 241000256856 Vespidae Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001715 carbamic acids Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000020004 porter Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Chemical group 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47233565A | 1965-07-15 | 1965-07-15 | |
| US55625966A | 1966-06-09 | 1966-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL26021A true IL26021A (en) | 1970-03-22 |
Family
ID=27043733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL26021A IL26021A (en) | 1965-07-15 | 1966-06-23 | Chroman-8-yl-carbamates,preparation thereof and pesticidal compositions containing them |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3468913A (enrdf_load_stackoverflow) |
| BE (1) | BE683813A (enrdf_load_stackoverflow) |
| BR (1) | BR6681282D0 (enrdf_load_stackoverflow) |
| CH (1) | CH476458A (enrdf_load_stackoverflow) |
| ES (2) | ES329148A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1153719A (enrdf_load_stackoverflow) |
| IL (1) | IL26021A (enrdf_load_stackoverflow) |
| NL (1) | NL6608777A (enrdf_load_stackoverflow) |
| OA (1) | OA02103A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES456574A1 (es) * | 1977-03-07 | 1978-02-16 | Rocador Sa | Procedimiento de obtencion de pentametil-carbamato de quer- cetina. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE567937A (enrdf_load_stackoverflow) * | 1957-05-23 | |||
| US3084182A (en) * | 1960-05-09 | 1963-04-02 | Mobay Chemical Corp | Blocked isocyanates from still residues |
| US3122551A (en) * | 1962-11-05 | 1964-02-25 | Abbott Lab | N-alkyl and n-aralkyl benzoxacycloalkaneamides |
| US3344170A (en) * | 1963-09-10 | 1967-09-26 | Dow Chemical Co | Hydrocarbonylene bis |
-
1966
- 1966-06-09 US US556259A patent/US3468913A/en not_active Expired - Lifetime
- 1966-06-23 IL IL26021A patent/IL26021A/en unknown
- 1966-06-23 NL NL6608777A patent/NL6608777A/xx unknown
- 1966-07-07 BE BE683813D patent/BE683813A/xx unknown
- 1966-07-12 OA OA52525A patent/OA02103A/xx unknown
- 1966-07-14 CH CH1021266A patent/CH476458A/de not_active IP Right Cessation
- 1966-07-14 BR BR181282/66A patent/BR6681282D0/pt unknown
- 1966-07-14 GB GB31661/66A patent/GB1153719A/en not_active Expired
- 1966-07-15 ES ES0329148A patent/ES329148A1/es not_active Expired
- 1966-10-25 ES ES0332731A patent/ES332731A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1153719A (en) | 1969-05-29 |
| DE1543603A1 (de) | 1971-03-18 |
| US3468913A (en) | 1969-09-23 |
| BR6681282D0 (pt) | 1973-12-26 |
| OA02103A (fr) | 1970-05-05 |
| CH476458A (de) | 1969-08-15 |
| ES332731A1 (es) | 1967-07-16 |
| ES329148A1 (es) | 1967-09-01 |
| NL6608777A (enrdf_load_stackoverflow) | 1967-01-16 |
| BE683813A (enrdf_load_stackoverflow) | 1967-01-09 |
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